Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean

ABSTRACT

The present invention relates to the use of use of a tetrazolinones for combating phytopathogenic fungi on soybean, such fungi containing a G143A mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors.

The present invention relates to the use of use of1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one(herein also referred to as compound I) for combating phytopathogenicfungi on soybean, such fungi containing a G143A mutation in themitochondrial cytochrome b gene conferring resistance to Qo inhibitors.

Qo inhibitor fungicides, often referred to as strobilurin-typefungicides (Sauter 2007: Chapter 13.2. Strobilurins and other complexIII inhibitors. In: Krämer, W.; Schirmer. U. (Ed.)—Modern CropProtection Compounds. Volume 2. Wiley-VCH Verlag 457-495), areconventionally used to control a number of fungal pathogens in crops. Qoinhibitors typically work by inhibiting respiration by binding to aubihydroquinone oxidation center of a cytochrome bc₁ complex (electrontransport complex III) in mitochondria. Said oxidation center is locatedon the outer side of the inner mitochrondrial membrane. A prime exampleof the use of Qo inhibitors includes the use of, for example,strobilurins on soybean for the control of Cercospora sojina, which isthe cause of frogeye leaf spot on soybeans. Unfortunately, widespreaduse of such Qo inhibitors has resulted in the selection of mutantpathogens which are resistant to such Qo inhibitors (Zeng et al., PLANTDISEASE 99(4), 544-550 (2015); Standish et al., PLANT DISEASE 99(10),1347-1352 (2015). Resistance to Qo inhibitors has been detected inseveral phytopathogenic fungi. In some pathogens, the major part ofresistance to Qo inhibitors in agricultural uses has been attributed topathogens containing a single amino acid residue substitution G143A inthe cytochrome b gene for their cytochrome bc₁ complex, the targetprotein of Qo inhibitors (see, for example Lucas, Pestic Outlook 14(6),268-70 (2003); and Fraaije et al., Phytopathol 95(8), 933-41 (2005).

In soybean, the following pathogens show increasing resistance towardsQo inhibitors due to their G143A mutation:

Cercospora sojina (frogeye leaf spot) and Corynespora cassiicola (targetspot).

Thus, new methods and compositions are desirable for controlling thesepathogen induced diseases in crops comprising plants subjected topathogens that are resistant to Qo inhibitors. Furthermore, in manycases, in particular at low application rates, the fungicidal activityof the known fungicidal strobilurin analogue compounds isunsatisfactory, especially in case that a high proportion of the fungalpathogens contain a mutation in the mitochondrial cytochrome b geneconferring resistance to Qo inhibitors. Based on this, it was also anobject of the present invention to provide compounds having improvedactivity and/or a broader activity spectrum against such resistantphytopathogenic harmful fungi on soybean.

“Qo inhibitor,” as used herein, includes any substance that is capableof diminishing and/or inhibiting respiration by binding to anubihydroquinone oxidation center of a cytochrome bc₁ complex inmitochondria. The oxidation center is typically located on the outerside of the inner mitochrondrial membrane.

From WO2013/092224, the use of Qo inhibitors is known for combatingphytopathogenic fungi that are resistant to Qo inhibitors is generallyknown. However, neither Cercospora sojina (frogeye leaf spot) andCorynespora cassiicola (target spot) as resistant pathogen nor thespecific compound of formula I are not explicitly disclosed therein.Thus, there is a constant need to find further compounds with evenimproved action against fungi that are resistant to Qo inhibitors on topof those disclosed in WO2013/092224.

The compounds I have surprisingly high action against Cercospora sojina(frogeye leaf spot) and Corynespora cassiicola (target spot) on soybean.

Thus, the present invention relates to the use of1-[2-[[1-(4-chlorophenyl)pyrazol3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one(herein also referred to as compound I) for combating phytopathogenicfungi containing a mutation in the mitochondrial cytochrome b geneconferring resistance to Qo inhibitors on soybean, wherein the mutationis G143A.

The present invention also relates to the use of a mixture comprisingcompound I in combination with a second compound II, wherein compound IIis selected from2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,prothioconazole, difenoconazole, propiconazole, tetraconazole,tebucoanzole, mancozeb, chlorothalonil, fluxapyroxad, bixafen,benzovindiflupyr, pydiflumetofen,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,penthiopyrad, isopyrazam, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,trifloxystrobin, picoxystrobin, azoxystrobin, mandestrobin,metominostrobin and fenpropimorph.

The present invention also relates to the use of a mixture comprisingcompound I in combination with two compounds II, wherein compound II isdefined above.

The fungi on soybean containing a G143A mutation in the mitochondrialcytochrome h gene conferring resistance to Qo inhibitors are hereinafterreferred to as “resistant fungi”. Resistant fungi on soybean in thecourse of the use of the present invention, wherein the mutation isG143A are Cercospora sojina (frogeye leaf spot) and Corynesporacassiicola (target spot).

Thus, in a preferred embodiment, the present invention relates to theuse of1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-onefor combating resistant fungi on soybean, wherein Y is Y1 and theresistant fungi is Cercospora sojina

In a further preferred embodiment, the present invention relates to theuse of a of1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-onefor combating resistant fungi on soybean, wherein Y is Y1 and theresistant fungi is Corynespora cassiicola.

The present invention also relates to the use of a mixture comprisingcompound I in combination with a second compound II, wherein compound IIis selected from2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,prothioconazole, difenoconazole, propiconazole, tetraconazole,tebucoanzole, mancozeb, chlorothalonil, fluxapyroxad, bixafen,benzovindiflupyr, pydiflumetofen,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethyindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,penthiopyrad, isopyrazam, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,trifloxystrobin, picoxystrobin, azoxystrobin, mandestrobin,metominostrobin and fenpropimorph for combating Cercospora sojina andCorynespora cassiicola on soybean.

In a further preferred embodiment, the present invention relates to theuse of any of the mixtures of compound I and compound II as definedabove for combating resistant fungi on soybean, wherein the resistantfungi is Corynespora cassiicola.

In a further preferred embodiment, the present invention relates to theuse of any of the mixtures of compound I and compound II as definedabove for combating resistant fungi on soybean, wherein the resistantfungi is Cercospora sojina.

Thus, the present invention relates to the use of any of the mixturesM-1 to M-31 as defined in Table 1 for combating resistant fungi onsoybean, and the resistant fungi is Corynespora cassiicola.

TABLE 1 “I” is compound I, “II” is compound II” No I II M-1 I2-[4-(4-chlorophenoxy)- 2- (trifluoromethyl)phenyl]- 1-(1,2,4-triazol-1-yl)propan-2-ol M-2 I 2-[4-(4-chlorophenoxy)- 2-(trifluoromethyl)phenyl]- 3-methyl-1-(1,2,4- triazol-1-yl)butan-2-ol M-3I 1-[4-(4-chlorophenoxy)- 2- (trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4- triazol-1-yl)ethanol M-4 I fluxapyroxad M-5 Ipyraclostrobin M-6 I (Z,2E)-5-[1-(2,4- dichlorophenyl)pyrazol-3-yl]¬oxy-2- methoxyimino-N,3- dimethyl-pent-3- enamide M-7 I(Z,2E)-5-[1-(4- chlorophenyl)pyrazol-3- yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3- enamide M-8 I fenpropimorph M-9 I prothioconazoleM-10 I difenoconazole M-11 I propiconazole M-12 I tetraconazole M-13 Itebucoanzole M-14 I mancozeb M-15 I chlorothalonil M-16 I bixafen M-17 Ibenzovindiflupyr M-18 I pydiflumetofen M-19 I 3-(difluoromethyl)-1-methyl-N-(1,1,3- trimethylindan-4- yl)pyrazole-4- carboxamide; M-20 I3-(trifluoromethyl)-1- methyl-N-(1,1,3- trimethylindan-4- yl)pyrazole-4-carboxamide; M-21 I 1,3-dimethyl-N-(1,1,3- trimethylindan-4-yl)pyrazole-4- carboxamide; M-22 I 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3- trimethylindan-4- yl)pyrazole-4- carboxamide; M-23 I3-(difluoromethyl)-1,5- dimethyl-N-(1,1,3- trimethylindan-4-yl)pyrazole-4- carboxamide; M-24 I 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4- yl)pyrazole-4- carboxamide M-25 I penthiopyradM-26 I isopyrazam M-27 I trifloxystrobin M-28 I picoxystrobin M-29 Iazoxystrobin M-30 I mandestrobin M-31 I metominostrobin

Thus, the present invention relates to the use of any of the mixturesM-1 to M-31 as defined in Table 1 for combating resistant fungi onsoybean, and the resistant fungi is Cercospora sojina.

In a more preferred embodiment, the present invention relates to the useof any of the mixtures of compound I and compound II for combatingresistant fungi on soybean, wherein compound II is selected from thegroup consisting of2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,fluxapyroxad, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamideand fenpropimorph, wherein the resistant fungi is Corynesporacassiicola.

In a most preferred embodiment, the present invention relates to the useof any of the mixtures of compound I and compound II for combatingresistant fungi on soybean, wherein compound II is selected from thegroup consisting of2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,prothioconazole, fluxapyroxad, metrafenone, pyraclostrobin andazoxystrobin, wherein the resistant fungi is Cercospora sojina.

Thus, the present invention relates to the use of any of the mixturesMB-1 to MB-8 as defined in Table 2 for combating resistant fungi onsoybean, and the resistant fungi is Corynespora cassiicola.

TABLE 2 “I” is compound I, “II” is compound II” No I II MB-1 I2-[4-(4-chlorophenoxy)- 2- (trifluoromethyl)phenyl]- 1-(1,2,4-triazol-1-yl)propan-2-ol MB-2 I 2-[4-(4-chlorophenoxy)- 2-(trifluoromethyl)phenyl]- 3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olMB-3 I 1-[4-(4-chlorophenoxy)- 2- (trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4- triazol-1-yl)ethanol MB-4 I fluxapyroxad MB-5 Ipyradostrobin MB-6 I (Z,2E)-5-[1-(2,4- dichlorophenyl)pyrazol-3-yl]¬oxy-2- methoxyimino-N,3- dimethyl-pent-3- enamide MB-7 I(Z,2E)-5-[1-(4- chlorophenyl)pyrazol-3- yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3- enamide MB-8 I fenpropimorph

Thus, the present invention relates to the use of any of the mixturesMB-1 to MB-48 as defined in Table 2 for combating resistant fungi onsoybean, wherein the resistant fungi is Cercospora sojina.

The present invention also relates to the use of a mixture comprisingcompound I in combination with a two compounds II selected from thegroup consisting of2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,prothioconazole, difenoconazole, propiconazole, tetraconazole,tebucoanzole, mancozeb, chlorothalonil, fluxapyroxad, bixafen,benzovindiflupyr, pydiflumetofen,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,penthiopyrad, isopyrazam, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,trifloxystrobin, picoxystrobin, azoxystrobin, mandestrobin,metominostrobin and fenpropimorph for combating resistant fungi onsoybean.

Thus, the present invention relates to the use of any of the mixturesM4A-1 to M4A-109 as defined in Table 3 to combat resistant fungi onsoybean, wherein the resistant fungi is Corynespora cassiicola.

TABLE 3 “I” is compound I, “II” is compound II” No I II II (2) M3A-1 I2-[4-(4-chlorophenoxy)-2- fluxapyroxad(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-2 I2-[4-(4-chlorophenoxy)-2- bixafen(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-3 I2-[4-(4-chlorophenoxy)-2- benzovindiflupyr(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-4 I2-[4-(4-chlorophenoxy)-2- pydiflumetofen(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-5 I2-[4-(4-chlorophenoxy)-2- 3-(difluoromethyl)-1-methyl-N-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- (1,1,3-trimethylindan-4-yl)propan-2-ol yl)pyrazole-4-carboxamide; M3A-6 I2-[4-(4-chlorophenoxy)-2- 3-(trifluoromethyl)-1-methyl-N-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- (1,1,3-trimethylindan-4-yl)propan-2-ol yl)pyrazole-4-carboxamide; M3A-7 I2-[4-(4-chlorophenoxy)-2- 1,3-dimethyl-N-(1,1,3-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-trimethylindan-4-yl)pyrazole-4- yl)propan-2-ol carboxamide; M3A-8 I2-[4-(4-chloraphenoxy)-2- 3-(trifluoromethyl)-1,5-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- dimethyl-N-(1,1,3-yl)propan-2-ol trimethylindan-4-yl)pyrazole-4- carboxamide; M3A-9 I2-[4-(4-chlorophenoxy)-2- 3-(difluoromethyl)-1,5-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- dimethyl-N-(1,1,3-yl)propan-2-ol trimethylindan-4-yl)pyrazole-4- carboxamide; M3A-10 I2-[4-(4-chlorophenoxy)-2- 1,3,5-trimethyl-N-(1,1,3-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-trimethylindan-4-yl)pyrazole-4- yl)propan-2-ol carboxamide M3A-11 I2-[4-(4-chlorophenoxy)-2- penthiopyrad(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-12 I2-[4-(4-chlorophenoxy)-2- isopyrazam(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-13 I2-[4-(4-chlorophenoxy)-2- pyraclostrobin(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-14 I2-[4-(4-chlorophenoxy)-2- (Z,2E)-5-[1-(2,4-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- dichlorophenyl)pyrazol-3-yl)propan-2-ol yl]¬oxy-2-methoxyimino-N,3- dimethyl-pent-3-enamideM3A-15 I 2-[4-(4-chlorophenoxy)-2- (Z,2E)-5-[1-(4-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-chlorophenyl)pyrazol-3-yl]oxy- yl)propan-2-ol2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-16 I2-[4-(4-chlorophenoxy)-2- trifloxystrobin(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-17 I2-[4-(4-chlorophenoxy)-2- picoxystrobin(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-18 I2-[4-(4-chlorophenoxy)-2- azoxystrobin(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-19 I2-[4-(4-chlorophenoxy)-2- mandestrobin(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-20 I2-[4-(4-chlorophenoxy)-2- metominosirobin(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-21 I2-[4-(4-chlorophenoxy)-2- mancozeb(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-22 I2-[4-(4-chlorophenoxy)-2- chlorothalonil(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-23 I2-[4-(4-chlorophenoxy)-2- fenpropimorph(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1- yl)propan-2-ol M3A-24 I2-[4-(4-chlorophenoxy)-2- fluxapyroxad(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-25 I 2-[4-(4-chlorophenoxy)-2- bixafen(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-26 I 2-[4-(4-chlorophenoxy)-2- benzovindiflupyr(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-27 I 2-[4-(4-chlorophenoxy)-2- pydiflumetofen(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-28 I 2-[4-(4-chlorophenoxy)-2- 3-(difluoromethyl)-1-methyl-N-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- (1,1,3-trimethylindan-4-triazol-1-yl)butan-2-ol yl)pyrazole-4-carboxamide; M3A-29 I2-[4-(4-chlorophenoxy)-2- 3-(trifluoromethyl)-1-methyl-N-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- (1,1,3-trimethylindan-4-triazol-1-yl)butan-2-ol yl)pyrazole-4-carboxamide; M3A-30 I2-[4-(4-chlorophenoxy)-2- 1,3-dimethyl-N-(1,1,3-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-trimethylindan-4-yl)pyrazole-4- triazol-1-yl)butan-2-ol carboxamide;M3A-31 I 2-[4-(4-chlorophenoxy)-2- 3-(trifluoromethyl)-1,5-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- dimethyl-N-(1,1,3-triazol-1-yl)butan-2-ol trimethylindan-4-yl)pyrazole-4- carboxamide;M3A-32 I 2-[4-(4-chlorophenoxy)-2- 3-(difluoromethyl)-1,5-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- dimethyl-N-(1,1,3-triazol-1-yl)butan-2-ol trimethylindan-4-yl)pyrazole-4- carboxamide;M3A-33 I 2-[4-(4-chlorophenoxy)-2- 1,3,5-trimethyl-N-(1,1,3-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-trimethylindan-4-yl)pyrazole-4- triazol-1-yl)butan-2-ol carboxamideM3A-34 I 2-[4-(4-chlorophenoxy)-2- penthiopyrad(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-35 I 2-[4-(4-chlorophenoxy)-2- isopyrazam(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-36 I 2-[4-(4-chlorophenoxy)-2- pyraclostrobin(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-37 I 2-[4-(4-chlorophenoxy)-2- (Z,2E)-5-[1-(2,4-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- dichlorophenyl)pyrazol-3-triazol-1-yl)butan-2-ol yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide M3A-38 I 2-[4-(4-chlorophenoxy)-2-(Z,2E)-5-[1-(4- (trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-chlorophenyl)pyrazol-3-yl]oxy- triazol-1-yl)butan-2-ol2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-39 I2-[4-(4-chlorophenoxy)-2- trifloxystrobin(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-40 I 2-[4-(4-chlorophenoxy)-2- picoxystrobin(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-41 I 2-[4-(4-chlorophenoxy)-2- azoxystrobin(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-42 I 2-[4-(4-chlorophenoxy)-2- mandestrobin(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-43 I 2-[4-(4-chlorophenoxy)-2- metominostrobin(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-44 I 2-[4-(4-chlorophenoxy)-2- mancozeb(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-45 I 2-[4-(4-chlorophenoxy)-2- chlorothalonil(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-46 I 2-[4-(4-chlorophenoxy)-2- fenpropimorph(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4- triazol-1-yl)butan-2-olM3A-47 I 1-[4-(4-chlorophenoxy)-2- fluxapyroxad(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-48 I 1-[4-(4-chlorophenoxy)-2- bixafen(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-49 I 1-[4-(4-chlorophenoxy)-2- benzovindiflupyr(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-50 I 1-[4-(4-chlorophenoxy)-2- pydiflumetofen(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-51 I 1-[4-(4-chlorophenoxy)-2- 3-(difluoromethyl)-1-methyl-N-(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,1,3-trimethylindan-4-(1,2,4-triazol-1-yl)ethanol yl)pyrazole-4-carboxamide; M3A-52 I1-[4-(4-chlorophenoxy)-2- 3-(trifluoromethyl)-1-methyl-N-(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,1,3-trimethylindan-4-(1,2,4-triazol-1-yl)ethanol yl)pyrazole-4-carboxamide; M3A-53 I1-[4-(4-chlorophenoxy)-2- 1,3-dimethyl-N-(1,1,3-(trifluoromethyl)phenyl]-1-cyclopropyl-2-trimethylindan-4-yl)pyrazole-4- (1,2,4-triazol-1-yl)ethanol carboxamide;M3A-54 I 1-[4-(4-chlorophenoxy)-2- 3-(trifluoromethyl)-1,5-(trifluoromethyl)phenyl]-1-cyclopropyl-2- dimethyl-N-(1,1,3-(1,2,4-triazol-1-yl)ethanol trimethylindan-4-yl)pyrazole-4- carboxamide;M3A-55 I 1-[4-(4-chlorophenoxy)-2- 3-(difluoromethyl)-1,5-(trifluoromethyl)phenyl]-1-cyclopropyl-2- dimethyl-N-(1,1,3-(1,2,4-triazol-1-yl)ethanol trimethylindan-4-yl)pyrazole-4- carboxamide;M3A-56 I 1-[4-(4-chlorophenoxy)-2- 1,3,5-trimethyl-N-(1,1,3-(trifluoromethyl)phenyl]-1-cyclopropyl-2-trimethylindan-4-yl)pyrazole-4- (1,2,4-triazol-1-yl)ethanol carboxamideM3A-57 I 1-[4-(4-chlorophenoxy)-2- penthiopyrad(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-58 I 1-[4-(4-chlorophenoxy)-2- isopyrazam(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-59 I 1-[4-(4-chlorophenoxy)-2- pyraclostrobin(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-60 I 1-[4-(4-chlorophenoxy)-2- (Z,2E)-5-[1-(2,4-(trifluoromethyl)phenyl]-1-cyclopropyl-2- dichlorophenyl)pyrazol-3-(1,2,4-triazol-1-yl)ethanol yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide M3A-61 I 1-[4-(4-chlorophenoxy)-2-(Z,2E)-5-[1-(4- (trifluoromethyl)phenyl]-1-cyclopropyl-2-chlorophenyl)pyrazol-3-yl]oxy- (1,2,4-triazol-1-yl)ethanol2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-62 I1-[4-(4-chlorophenoxy)-2- trifloxystrobin(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-63 I 1-[4-(4-chlorophenoxy)-2- picoxystrobin(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-64 I 1-[4-(4-chlorophenoxy)-2- azoxystrobin(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-65 I 1-[4-(4-chlorophenoxy)-2- mandestrobin(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-66 I 1-[4-(4-chlorophenoxy)-2- metominostrobin(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-67 I 1-[4-(4-chlorophenoxy)-2- mancozeb(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-68 I 1-[4-(4-chlorophenoxy)-2- chlorothalonil(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-69 I 1-[4-(4-chlorophenoxy)-2- fenpropimorph(trifluoromethyl)phenyl]-1-cyclopropyl-2- (1,2,4-triazol-1-yl)ethanolM3A-70 I fluxapyroxad prothioconazole M3A-71 I fiuxapyroxaddifenoconazole M3A-72 I fluxapyroxad propiconazole M3A-73 I fluxapyroxadtetraconazole M3A-74 I fluxapyroxad tebucoanzole M3A-75 I fluxapyroxadpyraclostrobin M3A-76 I fluxapyroxad (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide M3A-77 I fluxapyroxad (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy- 2-methoxyimino-N,3-dimethyl-pent-3-enamide M3A-78 I fluxapyroxad trifloxystrobin M3A-79 Ifluxapyroxad picoxystrobin M3A-80 I fluxapyroxad azoxystrobin M3A-81 Ifluxapyroxad mandestrobin M3A-82 I fluxapyroxad metominostrobin M3A-83 Ifluxapyroxad mancozeb M3A-84 I fluxapyroxad chlorothalonil M3A-85 Ifluxapyroxad fenpropimorph M3A-86 I pyraclostrobin prothioconazoleM3A-87 I pyraclostrobin difenoconazole M3A-88 I pyraclostrobinpropiconazole M3A-89 I pyraclostrobin tetraconazole M3A-90 Ipyraclostrobin tebucoanzole M3A-91 I pyraclostrobin mancozeb M3A-92 Ipyraclostrobin chlorothalonil M3A-93 I pyraclostrobin fenpropimorphM3A-94 I (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- prothioconazoleyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-95 I(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- difenoconazoleyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-96 I(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- propiconazoleyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-97 I(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- tetraconazoleyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-98 I(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- tebucoanzoleyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-99 I(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- mancozebyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-100 I(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- chlorothalonilyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-101 I(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3- fenpropimorphyl]¬oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide M3A-102 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- prothioconazoleyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide M3A-103 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- difenoconazoleyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide M3A-104 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- propiconazoleyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide M3A-105 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- tetraconazoleyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide M3A-106 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- tebucoanzoleyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide M3A-107 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- mancozebyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide M3A-108 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- chlorothalonilyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide M3A-109 I(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- fenpropimorphyl]oxy-2-methoxyimino-N,3-dimethyl-pent- 3-enamide

Thus, the present invention relates to the use of any of the mixturesM3A-1 to M3A-109 as defined in Table 43 for combating resistant fungi onsoybean, and the resistant fungi is Cercospora sojina.

All above-referred mixtures are herein below abbreviated as inventivemixtures.

The term “use of compound I or any of the inventive mixtures forcombating resistant fungi on soybean” comprises a method for controllingresistant fungi on soybean, wherein the fungi, their habitat, breedinggrounds, their locus or the plants to be protected against such fungalattack, the soil or plant propagation material (preferably seed) aretreated with a pesticidally effective amount of a compound I as definedabove or a mixture of compound I with one or two compounds II.

Preferably, such method for controlling resistant fungi on soybeancomprises treating the pest, their habitat, breeding grounds, theirlocus or the plants to be protected against pest attack with apesticidally effective amount of a compound I as defined above or amixture of compound I with one or two compounds II.

The term “effective amount” means that compound I or the inventivemixtures are used in a quantity which allows obtaining the desiredeffect which is a synergistic control of resistant fungi, but which doesnot give rise to any phytotoxic symptom on the treated plant.

If the compound I is applied with one or two compounds II, suchapplication can be made simultaneous that is jointly or separately, orin succession.

The ratio by weight of compound I and compound II in binary inventivemixtures is from 20000:1 to 1:20000, from 500:1 to 1:500, preferablyfrom 100:1 to 1:100 more preferably from 50:1 to 1:50, most preferablyfrom 20:1 to 1:20, and utmost preferably ratios from 10:1 to 1:10, whichalso includes ratios of 1:5 to 5:1, 1:1.

The ratio by weight of compound I, II and second compound II in eachcombination of two ingredients in the mixture of three ingredients isfrom 20000:1 to 1:20000, from 500:1 to 1:500, preferably from 100:1 to1:100 more preferably from 50:1 to 1:50, most preferably from 20:1 to1:20, and utmost preferably ratios from 10:1 to 1:10 including alsoratios from 1:5 to 5:1, or 1:1.

Compound I or the inventive mixtures can be accompanied by furtherpesticides, e.g. one or more insecticides, fungicides, herbicides.

The compound I or the inventive mixtures can be converted into customarytypes of agrochemical compositions, e. g. solutions, emulsions,suspensions, dusts, powders, pastes, granules, pressings, capsules,dispersions, and mixtures thereof. Examples for composition types aresuspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC),emulsions (e.g. EW, EO, ES, ME), dispersible concentrates (DC), capsules(e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP,SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR,FG, GG, MG), insecticidal articles (e.g. LN), as well as gelformulations for the treatment of plant propagation materials such asseeds (e.g. GF). These and further compositions types are defined in the“Catalogue of pesticide formulation types and international codingsystem”, Technical Monograph No. 2, 6^(th) Ed. May 2008, CropLifeInternational.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers,e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas;products of vegetable origin, e.g. cereal meal, tree bark meal, woodmeal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemulsifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-subsitituedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I or the inventive mixtures on the target.Examples are surfactants, mineral or vegetable oils, and otherauxiliaries. Further examples are listed by Knowles, Adjuvants andadditives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkyliso-thiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

-   i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of a compound I or the inventive mixture and 5-15 wt %wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/orin a water-soluble solvent (e.g. alcohols) ad 100 wt %. The activesubstance dissolves upon dilution with water.

-   ii) Dispersible Concentrates (DC)

5-25 wt % of a compound I or the inventive mixture and 1-10 wt %dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent(e.g. cyclohexanone) ad 100 wt %. Dilution with water gives adispersion.

-   iii) Emulsifiable Concentrates (EC)

15-70 wt % of a compound I or the inventive mixture and 5-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in water-insoluble organic solvent (e.g.aromatic hydrocarbon) ad 100 wt %. Dilution with water gives anemulsion.

-   iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I or the inventive mixture and 1-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent(e.g. aromatic hydrocarbon). This mixture is introduced into water ad100 wt % by means of an emulsifying machine and made into a homogeneousemulsion. Dilution with water gives an emulsion.

-   v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I or the inventivemixture are comminuted with addition of 2-10 wt % dispersants andwetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate),0.1-2 wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give afine active substance suspension. Dilution with water gives a stablesuspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

-   vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a compound I or the inventive mixture are ground finelywith addition of dispersants and wetting agents (e.g. sodiumlignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared aswater-dispersible or water-soluble granules by means of technicalappliances (e. g. extrusion, spray tower, fluidized bed). Dilution withwater gives a stable dispersion or solution of the active substance.

-   vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP,    WS)

50-80 wt % of a compound I or the inventive mixture are ground in arotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodiumlignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) andsolid carrier (e.g. silica gel) ad 100 wt %. Dilution with water gives astable dispersion or solution of the active substance.

-   viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I or the inventivemixture are comminuted with addition of 3-10 wt % dispersants (e.g.sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)and water ad 100 wt % to give a fine suspension of the active substance.Dilution with water gives a stable suspension of the active substance.

-   ix) Microemulsion (ME)

5-20 wt % of a compound I or the inventive mixture are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide andcyclohexanone), 10-25 wt % surfactant blend (e.g. alcohol ethoxylate andarylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1h to produce spontaneously a thermodynamically stable microemulsion.

-   x) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I or the inventivemixture, 0-40 wt % water insoluble organic solvent (e.g. aromatichydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate,methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radicalpolymerization initiated by a radical initiator results in the formationof poly(meth)acrylate microcapsules. Alternatively, an oil phasecomprising 5-50 wt % of a compound I or the inventive mixture accordingto the invention, 0-40 wt % water insoluble organic solvent (e.g.aromatic hydrocarbon), and an isocyanate monomer (e.g.diphenylmethene-4,4′-diisocyanatae) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). The additionof a polyamine (e.g. hexamethylenediamine) results in the formation ofpolyurea microcapsules. The monomers amount to 1-10 wt %. The wt %relate to the total CS composition.

-   xi) Dustable Powders (DP, DS)

1-10 wt % of a compound I or the inventive mixture are ground finely andmixed intimately with solid carrier (e.g. finely divided kaolin) ad 100wt %.

-   xii) Granules (GR, FG)

0.5-30 wt % of a compound I or the inventive mixture is ground finelyand associated with solid carrier (e.g. silicate) ad 100 wt %.Granulation is achieved by extrusion, spray-drying or fluidized bed.

-   xiii) Ultra-Low Volume Liquids (UL)

1-50 wt % of a compound I or the inventive mixture are dissolved inorganic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xiii) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The resulting agrochemical compositions generally comprise between 0.01and 95%, preferably between 0.1 and 90%, and in particular between 0.5and 75%, by weight of active substance. The active substances areemployed in a purity of from 90% to 100%, preferably from 95% to 100%(according to NMR spectrum).

Solutions for seed treatment (LS), Suspoemulsions (SE), flowableconcentrates (FS), powders for dry treatment (DS), water-dispersiblepowders for slurry treatment (WS), water-soluble powders (SS), emulsions(ES), emulsifiable concentrates (EC) and gels (GF) are usually employedfor the purposes of treatment of plant propagation materials,particularly seeds. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40%, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying the compound I or the inventive mixtures andcompositions thereof, respectively, on to plant propagation material,especially seeds include dressing, coating, pelleting, dusting, soakingand in-furrow application methods of the propagation material.Preferably, the compound I or the inventive mixtures or the compositionsthereof, respectively, are applied on to the plant propagation materialby a method such that germination is not induced, e. g. by seeddressing, pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.01to 1.0 kg per ha, and in particular from 0.05 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. bydusting, coating or drenching seed, amounts of active substance of from0.01-10 kg, preferably from 0.1-1000 g, more preferably from 1-100 g per100 kilogram of plant propagation material (preferably seeds) aregenerally required.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, ifappropriate not until immediately prior to use (tank mix). These agentscan be admixed with the compositions according to the invention in aweight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank orany other kind of vessel used for applications (e. g. seed treaterdrums, seed pelleting machinery, knapsack sprayer) and furtherauxiliaries may be added, if appropriate.

Consequently, one embodiment of the invention is a kit for preparing ausable pesticidal composition, the kit comprising a) a compositioncomprising component 1) as defined herein and at least one auxiliary;and b) a composition comprising component 2) as defined herein and atleast one auxiliary; and optionally c) a composition comprising at leastone auxiliary and optionally one or two further active components II asdefined herein above.

1-8. (canceled)
 9. A method for controlling phytopathogenic fungi onsoybean comprising treating the fungi, their habitat, breeding grounds,their locus or the plants to be protected against fungal attack, thesoil or plant propagation material with an effective amount of1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one,as compound I, or a composition comprising compound I.
 10. The method ofclaim 9, wherein the phytopathogenic fungi is Cercospora sojina.
 11. Themethod of claim 9, wherein the phytopathogenic fungi is Corynesporacassiicola.
 12. The method of claim 9, wherein compound I is applied inform of a composition comprising compound I and compound II, whereincompound II is selected from the group consisting of2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,prothioconazole, difenoconazole, propiconazole, tetraconazole,tebucoanzole, mancozeb, chlorothalonil, fluxapyroxad, bixafen,benzovindiflupyr, pydiflumetofen,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,penthiopyrad, isopyrazam, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,trifloxystrobin, picoxystrobin, azoxystrobin, mandestrobin,metominostrobin and fenpropimorph.
 13. The method of claim 12, whereincompound II is selected from the group consisting of2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,fluxapyroxad, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamideand fenpropimorph.
 14. The method of claim 12, wherein the ratio byweight of compound I and second compound II is 500:1 to 1:500.
 15. Themethod of claim 12, wherein the ratio by weight of compound I and secondcompound II is 100:1 to 1:100.
 16. The method of claim 9, wherein saidfungi contains a G143A mutation in the mitochondrial cytochrome b geneconferring resistance to Qo inhibitors.
 17. The method of claim 16,wherein compound I is applied in form of a composition comprisingcompound I and compound II, wherein compound II is selected from thegroup consisting of2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,prothioconazole, difenoconazole, propiconazole, tetraconazole,tebucoanzole, mancozeb, chlorothalonil, fluxapyroxad, bixafen,benzovindiflupyr, pydiflumetofen,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,penthiopyrad, isopyrazam, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,trifloxystrobin, picoxystrobin, azoxystrobin, mandestrobin,metominostrobin and fenpropimorph.
 18. The method of claim 17, whereincompound II is selected from the group consisting of2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,fluxapyroxad, pyraclostrobin,(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]¬oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamideand fenpropimorph.
 19. The method of claim 17, wherein the ratio byweight of compound I and second compound II is 500:1 to 1:500.
 20. Themethod of claim 17, wherein the ratio by weight of compound I and secondcompound II is 100:1 to 1:100.